South Side Vacation Rentals

"Great amount of space, awesome location. Super friendly and great to book with! Will definitely look for this place again next time I'm in town."

"I love that when I walked in it smelled like cleaner. It was a very steep walk upstairs, but other than that, everything else was pretty great. No handicap access."

"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"

"Great location, ample space & good communication throughout stay."

"This was exactly what we were looking for! Great location and will stay anytime I’m in Chicago!"

"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."

"Dans place was perfect. You can’t beat the location — a beautiful brownstone in one of the best parts of the city. It had everything we needed. Will definitely be back!"

"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."

"Space was great and ability to host a girls weekend was perfect! Thank you."

"The ceilings are tall and space is welcoming. The tile in the shower was really cool and the towels were perfect. It was nice to have an open kitchen available but I did not need it as the food in the neighborhood was so yummy. The bed was awesome and the pillow was incredible. To top it off a client came over and we played pool. Another thing I enjoyed was the shoes at the door policy… clean spaces start with no shoes and this place is clean and stylish. Great location and I am happy to give...

"Staying at this VRBO house in Chicago was an absolute knockout! The location was perfect for catching the wrestling show with my friends, and the house itself was spacious, clean, and had all the amenities we needed. From comfy beds to a fully equipped kitchen, we felt right at home. The host was super accommodating and made check-in a breeze. Definitely a five-star experience – would book again in a heartbeat!"

"Property was just as described, clean and plenty of space! Location was perfect if you’re thinking of going to a Cubs game! Target literally next door and plenty of restaurants in walking distance! Host was great and even checked in with us during our stay. Would return!"

"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."

"This property was a very very nice place. Very comfortable and cozy. The backyard is great for kids since it’s all fenced in. Simple and quick drive to the dunes. Nice place to come back to after a long hot day at the beach! ❤️"

"The home was very comfortable - it was modern and the beds were good. Unfortunately the repairs to make it rentable were not high quality. The bathroom sink in the half bath was leaking when we arrived. The door frame of the basement bathroom had fallen off & was lying on the floor when we arrived. The shower door in the upstairs bathroom would not stay on the track. However , none of these problems would deter me from renting again. They were just inconveniences."

"Had 5 old 65+ year old college friends into town for a Cubs game, card playing, reuniting big eating weekend. The house was perfect. Very clean and presentable with every amenity we were looking for. 5-star place. Thank you very much!!!!"

"Perfect house for a large group! There are plenty of beds and bathrooms. The location is awesome. The host was super attentive and checked in frequently without being annoying. We had an awesome time!"

"It was very clean! The parking can be difficult, but otherwise no complaints! Very close to restaurants and shopping. "

"Place was as described and worked perfect for our stay."

"Good location! Very clean! Easy to find free parking!"